The Exchanges

Q What do you do? What do you do? Sorry. What if you do, if you wouldn't, But they're not bad. They're okay.

A Yeah. Yeah. In many cases that, that can happen. I think ultimately depends on the kind of company you want to, you want to run. We want people who we want to rehire. And if someone's fine, but not quite right, they're better off finding another opportunity somewhere else where, where they're perfect for the, for the job. So sometimes there's these really hard decisions that are made around that period of time about like, this person's cutting it. They're fine. They're, they're good even, but they're not quite right for us. It's not that they're not quite right for them. It's that they're not quite right for us. And given the choice, we probably would not hire this person again. Um, knowing what we know now could be cultural fit, could be skills, could be a lot of different things. They may have come in at a level where we thought they were better than they were going to be. Maybe they'll be that good in three or four years, but when you can just hire someone else instead, like maybe that's the choice. So that's what the first year is really about. It's like, is this person gonna, gonna fit in here, and are they, are they on a trajectory that makes sense where we would hire them again? That's, that's the, that's the gist of it. There's a lot of nuance in it, of course, but that's the gist of it.

AI assessment note: “if someone's fine, but not quite right, they're better off finding another opportunity”

Q matters, and it's where your business will always be ultimately, even if it's not today. Yes. Dharmesh at HubSpot says differently. I'm intrigued to hear your thoughts on this in terms of, does that have to be the way in SaaS? And if so, how do you think about advising founders on When is the right time or if they need to at all go up market into massive enterprise?

A Well, again, it comes down to what are your economics? So I'm just making up numbers here. Let's say it costs us five million bucks a year on our business. I want to make six. That's good. It's not about scaling up or scaling down. It's covering your costs and then coming out with a profit on top of that. Like that's it. This idea of Scaling like for what reason and to what end and where are you going with it? Like I, there's so many companies scaling and losing their ass. That doesn't seem like a good plan. They're getting bigger and bigger and bigger. And so are their losses. So like I, that doesn't work. I don't see what that means. And, and if they follow the same path, they're going to keep losing more and more and more because they're unprofitable per customer. So it's like this idea of scale has never been something that really made any sense to me. What makes sense to me is how do you operate profitably? Um, that's, that's how I know how to run a business. Uh, and it might mean we've left plenty of opportunities on the table, or we could have been bigger and all these things, but bigger to what, for what reason? Again, like, I don't want to be bigger and have much lower margins. I don't want to be bigger and lose money per customer. I don't want to be bigger and have to take a bunch of money to support that growth. Like, I don't want any of those things. Um, and so my, …

AI assessment note: “It's not about scaling up or scaling down. It's covering your costs and then coming”

Q How do you feel about kind of what is measured improves and also kind of driving teams with goals?

A Um, I'm not a goal driven person, so I don't drive teams with goals. Uh, I don't have goals really. I don't really believe in that. I know a lot of people do, but it's not my thing. It's never been my thing. My thing is like, do the best job that you can. And why wouldn't you just do that? Like, what is it about the goal that makes you do the best you can? I think you should be, you know, intrinsically motivated to simply do the best you can. Um, So that, that's sort of my approach. There's not like a thing that I would do differently if, if there was some number ahead of me. In fact, I probably would hate it more because now I'm chasing something that's arbitrary, ultimately. I mean, people set up these targets and that we've done in the past, you set up some target and you aim for it. It's like, why do we pick that number? Well, it happens to be a nice round number. So like, I'm, I'm, everything I'm doing now is, is based on some made up number that happens to be a nice pretty round number. Like, And, and the, and the stress I'm taking on and the challenges we have are all based on this thing that we made up. Like, how about we don't make anything up and just do the best work we can on a daily basis. And that adds up and let the chips fall where they may. I mean, that's kind of my, that's my approach, you know, for better or for worse.

AI assessment note: “I'm not a goal driven person, so I don't drive teams with goals.”

Q What do you do? What do you do? Sorry. What if you do, if you wouldn't, But they're not bad. They're okay.

A Yeah. Yeah. In many cases that, that can happen. I think ultimately depends on the kind of company you want to, you want to run. We want people who we want to rehire. And if someone's fine, but not quite right, they're better off finding another opportunity somewhere else where, where they're perfect for the, for the job. So sometimes there's these really hard decisions that are made around that period of time about like, this person's cutting it. They're fine. They're, they're good even, but they're not quite right for us. It's not that they're not quite right for them. It's that they're not quite right for us. And given the choice, we probably would not hire this person again. Um, knowing what we know now could be cultural fit, could be skills, could be a lot of different things. They may have come in at a level where we thought they were better than they were going to be. Maybe they'll be that good in three or four years, but when you can just hire someone else instead, like maybe that's the choice. So that's what the first year is really about. It's like, is this person gonna, gonna fit in here, and are they, are they on a trajectory that makes sense where we would hire them again? That's, that's the, that's the gist of it. There's a lot of nuance in it, of course, but that's the gist of it.

AI assessment note: “if someone's fine, but not quite right, they're better off finding another opportunity”

Q What do you think of the current VC ecosystem? We see these price rounds at, you know, billion dollars for pre-revenue companies. We see huge funding rounds. We just so much, frankly.

A This is a softball. I mean, I don't understand it. I'm very much like an economics one-on-one kind of Basic guy when it comes to this, like, companies that make money are, I think, great companies. I mean, they can do bad things, but, like, economically, great companies. Make more money than you spend. I'm into that. Figure out how to make money later. Not so much into that, and I really don't understand those kind of valuations, so it just doesn't make sense to me. I'm sure I've missed many opportunities getting involved with some of them. For example, like, Clubhouse is a great example of this right now. I am exceptionally bullish on Clubhouse, more so than I've been about any company I've seen in a long time, yet... They don't make a penny. They're probably losing a ton of money because like it's expensive to do what they do. And I know they'll probably figure this out down the road, but they are a company I would actually bet on, even though they go against my fundamental principles of like, come on, a business model is part of your business. Figure that part out. So there's always exceptions, but generally I don't get it. I don't get it. It doesn't make any sense to me.

AI assessment note: “I really don't understand those kind of valuations, so it just doesn't make sense”

Q Final one, I promise, and then we'll do a quick fire, but you know, obviously you mentioned your two children now, um, And there's a lot you now know that you didn't know when you had them. If you were to advise me or a younger self on being a good father, what do you know now that you wish you'd known or you'd advise your younger self?

A Well, I, what I've kind of come to realize, there's a couple like fundamental things about kids, but kids are, we have two, so I've seen that how just completely different they are. And again, just like I said earlier, art or management is the art of the individual. Parenting is as well. Like our daughter needs different things than our son. Um, and, and, and like, and vice versa. So I think it's, it's very much paying attention to, to each individual and how they are, um, and not trying to sort of blanket, have a blanket way of being. Um, that's, that's kind of something I think that's very important. I think the other thing is, um, um, follow their curiosity is something that's really helped me, um, discover new things. Um, Kids are incredibly curious and they also, you know, they actually, you know what, let me, that's true, but there's one thing that comes to mind right now, which is one of the fundamental things you learn when you have kids is that you cannot make people do things they don't want to do. I mean, you can really kind of make a kid get in the car if they need to things, but you, you can see fundamentally that it's incredibly hard and there's a lot of negative externalities when you try to force people to do anything they don't want to do. I think that comes, that comes through in business. It comes through in life. It comes through with your kids, but your kid…

AI assessment note: “Parenting is as well. Like our daughter needs different things than our son.”

Q Um, I don't like giving bad performance reviews. I don't like criticizing people. Can I ask, having done this for 23 years, what advice would you give me on giving effective negative feedback? Not necessarily firing someone, But Jason, the work is not up to scratch. Continuously, you've let me down, and it needs to get better. How, how do you advise me? Is it a shit sandwich? Help me.

A Yeah, I mean, it's, it's not easy. I'm not great at it either. I think the best thing is to be very direct and show examples. So when you, when you say to someone like, your work's not up to scratch or whatever, it's like, well, why not? So let's go through a few projects. Let's talk about a few things that happened. And, um, I think the more specific you get, The better off the feedback's gonna be, and the more someone can actually internalize it. Because if it's abstract, it's not to snuff, the quality isn't quite there, whatever, it's, it's just not enough to go on. So we tend to review projects, and we're always trying to look at real things here. When we hire people, we actually hire them first for a week, ah, on a contract basis, one week, not in every position, but in some, to actually do a project for us. And then we can actually look at real work together, discuss real work together to decide whether or not we can actually work together. So we're always trying to look at real stuff as much as we possibly can. I don't really care about resumes. I don't really care about a lot of that people's history. I don't care where they went to school. If they went to school, I don't care about any of those things. Let's look at the work itself. And so the same thing is true. If you're giving someone feedback, that's not great, or I mean, it can be helpful, but it may not be great …

AI assessment note: “I think the best thing is to be very direct and show examples.”

Q Final one, I promise, and then we'll do a quick fire, but you know, obviously you mentioned your two children now, um, And there's a lot you now know that you didn't know when you had them. If you were to advise me or a younger self on being a good father, what do you know now that you wish you'd known or you'd advise your younger self?

A Well, I, what I've kind of come to realize, there's a couple like fundamental things about kids, but kids are, we have two, so I've seen that how just completely different they are. And again, just like I said earlier, art or management is the art of the individual. Parenting is as well. Like our daughter needs different things than our son. Um, and, and, and like, and vice versa. So I think it's, it's very much paying attention to, to each individual and how they are, um, and not trying to sort of blanket, have a blanket way of being. Um, that's, that's kind of something I think that's very important. I think the other thing is, um, um, follow their curiosity is something that's really helped me, um, discover new things. Um, Kids are incredibly curious and they also, you know, they actually, you know what, let me, that's true, but there's one thing that comes to mind right now, which is one of the fundamental things you learn when you have kids is that you cannot make people do things they don't want to do. I mean, you can really kind of make a kid get in the car if they need to things, but you, you can see fundamentally that it's incredibly hard and there's a lot of negative externalities when you try to force people to do anything they don't want to do. I think that comes, that comes through in business. It comes through in life. It comes through with your kids, but your kid…

AI assessment note: “Parenting is as well. Like our daughter needs different things than our son.”

Q Um, I don't like giving bad performance reviews. I don't like criticizing people. Can I ask, having done this for 23 years, what advice would you give me on giving effective negative feedback? Not necessarily firing someone, But Jason, the work is not up to scratch. Continuously, you've let me down, and it needs to get better. How, how do you advise me? Is it a shit sandwich? Help me.

A Yeah, I mean, it's, it's not easy. I'm not great at it either. I think the best thing is to be very direct and show examples. So when you, when you say to someone like, your work's not up to scratch or whatever, it's like, well, why not? So let's go through a few projects. Let's talk about a few things that happened. And, um, I think the more specific you get, The better off the feedback's gonna be, and the more someone can actually internalize it. Because if it's abstract, it's not to snuff, the quality isn't quite there, whatever, it's, it's just not enough to go on. So we tend to review projects, and we're always trying to look at real things here. When we hire people, we actually hire them first for a week, ah, on a contract basis, one week, not in every position, but in some, to actually do a project for us. And then we can actually look at real work together, discuss real work together to decide whether or not we can actually work together. So we're always trying to look at real stuff as much as we possibly can. I don't really care about resumes. I don't really care about a lot of that people's history. I don't care where they went to school. If they went to school, I don't care about any of those things. Let's look at the work itself. And so the same thing is true. If you're giving someone feedback, that's not great, or I mean, it can be helpful, but it may not be great …

AI assessment note: “I think the best thing is to be very direct and show examples.”

Q is them, not me. You can hate them. Uh, so you mentioned like, you know, someone else will get those customers if, They don't. One question that I got was, I'd love to hear his thoughts on, I've really gained in confidence I'm asking this. Uh, they said, how did you lose your head start in every product to Atlassian? Is that fair? And how do you feel about that?

A Um, I don't really know what that means. So I think that there's a lot of customers out there. Um, there are a lot of companies out there and we get customers flooding to us from JIRA all the time. And I'm sure JIRA gets customers that are coming from us all the time. There's a, you know, a, a, a, a transfer all the time. People trying this, trying that. They try something for a while. It doesn't work. They try this for a while. They come back and forth. So the thing is, is it, it doesn't matter to us. What other people, how other people are doing in terms of the number of customers they have. This is, I think something entrepreneurs get wrong all the time. They, they compare themselves to someone else and they go, how many customers do they have? How many customers do they have? All that matters is do we have enough customers to make our own business work? That's all that matters. So I'm happy to see Atlassian, JIRA, uh, Trello, whatever their products do well. That's great. We can do well. They can do well. This is not a zero sum game. We have our own economics. They have their own economics. As long as we can make our economics work, which we have, we've been profitable for 23 years, every year. It doesn't matter how many we have versus how many they have. All that matters is can we make our business work? So I don't, I don't really, I don't care about any of those things. U…

AI assessment note: “I don't care about any of those things.”

Q quick fire because I'm aware I stupidly named it. But I'm going to say a short statement. You're going to hit me with your immediate thoughts in terms of like favorite book and all that shit. What was the last bit of content that actually really stuck with you? Could be magazine, could be TV show, could be movie, could be book, but that actually changed the way you think.

A I listened to, uh, I recently re-listened to Pink Floyd, Dark Side of the Moon. Um, on some mushrooms, and that was a really extraordinary experience actually. Um, I, I, I heard, it was interesting reminder that the thing that you, the thing that you think, you know, uh, you can, you can, um, experience in a different way. Uh, and, and that, that was just an example of that, but I've taken that experience and thought about that in terms of pretty much everything that I'm, you get very used to like the, the one note of something that you really know. And it turns out that there's, there's a lot of notes and a lot of angles on things that, that, that you're even, you know, that you think, you know, inside and out. So that was something that was a, a quite, uh, an interesting experience.

AI assessment note: “I recently re-listened to Pink Floyd, Dark Side of the Moon.”

Q is them, not me. You can hate them. Uh, so you mentioned like, you know, someone else will get those customers if, They don't. One question that I got was, I'd love to hear his thoughts on, I've really gained in confidence I'm asking this. Uh, they said, how did you lose your head start in every product to Atlassian? Is that fair? And how do you feel about that?

A Um, I don't really know what that means. So I think that there's a lot of customers out there. Um, there are a lot of companies out there and we get customers flooding to us from JIRA all the time. And I'm sure JIRA gets customers that are coming from us all the time. There's a, you know, a, a, a, a transfer all the time. People trying this, trying that. They try something for a while. It doesn't work. They try this for a while. They come back and forth. So the thing is, is it, it doesn't matter to us. What other people, how other people are doing in terms of the number of customers they have. This is, I think something entrepreneurs get wrong all the time. They, they compare themselves to someone else and they go, how many customers do they have? How many customers do they have? All that matters is do we have enough customers to make our own business work? That's all that matters. So I'm happy to see Atlassian, JIRA, uh, Trello, whatever their products do well. That's great. We can do well. They can do well. This is not a zero sum game. We have our own economics. They have their own economics. As long as we can make our economics work, which we have, we've been profitable for 23 years, every year. It doesn't matter how many we have versus how many they have. All that matters is can we make our business work? So I don't, I don't really, I don't care about any of those things. U…

AI assessment note: “This is not a zero sum game. We have our own economics.”

Q Tell me, which leader do you look up to and why?

A I know this is kind of a cop-out, but I mean it. Like, it's more of a hybrid. I don't look at a Person. I look at character traits of different people, and I respect those individual bits of different individuals, so there's not like a leader. That said, like, I like leaders who are very straightforward, so when I think about that, I think about people like Charlie Munger. Jeff Bezos is a very clear thinker and explainer. Anyone who can just, you hear what they're saying, or you read it and go, I got it. That's the kind of general leader that inspires me, but also the other one, I guess, would be somebody who helps people get better at what they do. That's What I'm trying to do more now is, is trying to help people grow versus like me growing. I grow by helping other people grow. That's not a great answer to your question because it's not specific, but that's all that came to mind, to be honest.

AI assessment note: “when I think about that, I think about people like Charlie Munger. Jeff Bezos”

Q What's an example of, do we even need to make a decision?

A There's probably, I'm trying to think of a, of a concrete example. This comes up all the time in software, which is a little bit, going to be a bit abstract, but, or a bit inside, because it's sort of hard to explain completely, but there's a bunch of features, let's say you're making a feature of some sort, and you, you're worried about, like, should we have the, should we have a button that does this, or a confirmation that does that, or, um, you know, should we explain this this way? Do we need a video to, you know, all these All this extra stuff that may not actually ultimately matter in the end, but there's a lot of discussion about it, a lot of, a lot of consternation about it, a lot of extra work involved with it, and sometimes you're like, you know what, it's just like, what if we just don't do this and see if anyone has any problems? I'll give you, actually here's a good example of this, um, specific just came to mind. Hey World, which is our, our, our, so we have an email service called hey, hey.com, h-e-y.com, and everyone who uses hey.com also gets a personal blog. And to post to the blog, you just email worldathey.com and whatever you write there, it goes on your personal blog. It's published instantly. We had this big fear initially when we were launching this. It's like, gosh, um, like, do we need to have content moderating and do we need to approve posts and wan…

AI assessment note: “do we need to have content moderating and do we need to approve posts”

Q What's an example of, do we even need to make a decision?

A There's probably, I'm trying to think of a, of a concrete example. This comes up all the time in software, which is a little bit, going to be a bit abstract, but, or a bit inside, because it's sort of hard to explain completely, but there's a bunch of features, let's say you're making a feature of some sort, and you, you're worried about, like, should we have the, should we have a button that does this, or a confirmation that does that, or, um, you know, should we explain this this way? Do we need a video to, you know, all these All this extra stuff that may not actually ultimately matter in the end, but there's a lot of discussion about it, a lot of, a lot of consternation about it, a lot of extra work involved with it, and sometimes you're like, you know what, it's just like, what if we just don't do this and see if anyone has any problems? I'll give you, actually here's a good example of this, um, specific just came to mind. Hey World, which is our, our, our, so we have an email service called hey, hey.com, h-e-y.com, and everyone who uses hey.com also gets a personal blog. And to post to the blog, you just email worldathey.com and whatever you write there, it goes on your personal blog. It's published instantly. We had this big fear initially when we were launching this. It's like, gosh, um, like, do we need to have content moderating and do we need to approve posts and wan…

AI assessment note: “I'll give you, actually here's a good example of this, um, specific just came to mind. Hey World”

Q Well, I'm interested, you know, naturally, um, as a single dude, uh, looking, you know, to find love also, um, that's very different to being a great husband. Time apart in this way would be challenging for a marriage. Um, what have been your lessons on really being a great husband and having a great marriage?

A Well, um, you'd have to ask my wife. I'm a great husband. We've been married for nine years. I think we're doing pretty well. We have two kids. I think it's, you know, um, my, my parents, when we got married, my parents wrote this really little short letter to us. Um, and, um, and there was a little bit of advice in, in the letter and I'm trying to remember exactly what it was, but it was, um, give each other space is, is a primary fundamental thing. Um, and, you know, compromise, but also give each other space. Um, and, and, and that, that I think is a really important thing. Um, now, not everyone's that way. I think you have to know who you are. Um, but, um, you know, um, if, if you, if you're someone who needs quiet time to recharge, or your wife is, or your spouse is, or whatever, you need to give them that, even if that's not what you want. You know, really understanding what the other person needs is incredibly important in relationship. I think, you know, it's not really this idea of, Of, um, you know, we're, we're, we're, as humans, we're very egocentric, and we're always thinking about ourselves first, and relationship is really about us. It's, it's not about you.

AI assessment note: “give each other space is, is a primary fundamental thing”

Q I think it's a bit like inputs and outputs, and actually the output is the goal. And actually what drives the output is the inputs, which is what really matters, which is what you're analyzing there. Do you see what I mean? The code quality.

A Yeah, it's the inputs that I'm, I mean, part of this too is like, um, one of the things we do is the first year is kind of a real big, I would say, I mean, people are hired, but it's kind of a test. The main question we ask at the end of the first year is would I hire this person again? That's the real question that we ask after the first year. And we don't ask it out loud, but that's kind of what managers are asking themselves. And that question sums up a whole bunch of things. Um, and it's a, it's like, you know, you inherently know the answer to that question if you are, uh, working with someone closely.

AI assessment note: “Yeah, it's the inputs that I'm, I mean, part of this too”

Q I think it's a bit like inputs and outputs, and actually the output is the goal. And actually what drives the output is the inputs, which is what really matters, which is what you're analyzing there. Do you see what I mean? The code quality.

A Yeah, it's the inputs that I'm, I mean, part of this too is like, um, one of the things we do is the first year is kind of a real big, I would say, I mean, people are hired, but it's kind of a test. The main question we ask at the end of the first year is would I hire this person again? That's the real question that we ask after the first year. And we don't ask it out loud, but that's kind of what managers are asking themselves. And that question sums up a whole bunch of things. Um, and it's a, it's like, you know, you inherently know the answer to that question if you are, uh, working with someone closely.

AI assessment note: “Yeah, it's the inputs that I'm, I mean, part of this too is”